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Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6
Abstract
The antineoplastic constituents of Combretum caffrum (Eckl. and Zeyh) Kuntze (Combretaceae family), a species indigenous to South Africa, have been investigated. Subsequently we isolated a series of closely related bibenzyls, stilbenes, and phenanthrenes from C. caffrum. Some of the stilbenes proved to be potent antimitotic agents which inhibited both tubulin polymerization and the binding of colchicine to tubulin. Combretastatin A-4 has been shown to be the most potent cancer cell growth inhibitor of the series. Presently this cis-stilbene is the most effective inhibitor of colchicine binding to tubulin and the simplest natural product yet described with such potent antitubulin effects. Combretastatin A-4, A-5, and A-6 were also found to inhibit growth of Neisseria gonorrhoeae. Details of the isolation and syntheses of combretastatins A-4 (2a), A-5 (2c), and A-6 (3a) have been described.
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Cited by
Messaoudi, S., Tréguier, B., Hamze, A., Provot, O., Peyrat, J.-F., De Losada, J. R., Liu, J.-M., Bignon, J., Wdzieczak-Bakala, J., Thoret, S., et al. (2009) · Journal of Medicinal Chemistry · doi:10.1021/jm900321u · Cited by 287
Anticancer agents from medicinal plants
Shoeb, M. (2008) · Bangladesh Journal of Pharmacology · doi:10.3329/bjp.v1i2.486 · Cited by 256
Mans, D. R. A., Rocha, A. B., & Schwartsmann, G. (2000) · The Oncologist · doi:10.1634/theoncologist.5-3-185 · Cited by 254
Metadata
- Authors
- Pettit, G. R., Singh, S. B., Boyd, M. R., Hamel, E., Pettit, R. K., Schmidt, J. M., & Hogan, F.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1995-05
- Volume
- 38
- Issue
- 10
- Pages
- 1666-1672
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1985036211
- Cited by
- 396
- References
- 0
- FWCI
- 1.30
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6. https://app.cochat.ai/papers/10.1021/jm00010a011
- The paper
- Pettit, G. R., Singh, S. B., Boyd, M. R., Hamel, E., Pettit, R. K., Schmidt, J. M., & Hogan, F. (1995). Antineoplastic Agents. 291. Isolation and Synthesis of Combretastatins A-4, A-5, and A-6. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00010a011
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